ES8708207A1 - Preparation process of alpha-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof. - Google Patents

Preparation process of alpha-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof.

Info

Publication number
ES8708207A1
ES8708207A1 ES553331A ES553331A ES8708207A1 ES 8708207 A1 ES8708207 A1 ES 8708207A1 ES 553331 A ES553331 A ES 553331A ES 553331 A ES553331 A ES 553331A ES 8708207 A1 ES8708207 A1 ES 8708207A1
Authority
ES
Spain
Prior art keywords
methyl ester
hydrochloride
aspartyl
alpha
dioxo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES553331A
Other languages
Spanish (es)
Other versions
ES553331A0 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP60066097A external-priority patent/JPS61225196A/en
Priority claimed from JP60066665A external-priority patent/JPH0751596B2/en
Application filed by Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Publication of ES8708207A1 publication Critical patent/ES8708207A1/en
Publication of ES553331A0 publication Critical patent/ES553331A0/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/801—Peptide sweetners

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Disclosed herein is a process for preparing alpha -L-aspartyl-L-phenylalanine methyl ester or its hydrochloride from 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester, prepared without using L-penylalanine methyl ester which involves problems in its stability, as a raw material. Specifically, the process comprises: bringing 5-benzyl-3,6-dioxo-2-piperazine acetic acid in the presence of methanol or 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester in the presence or absence of methanol into contact with hydrochloric acid isolating the thereby deposited alpha -L-aspartyl-L-phenylalanine methyl ester hydrochloride and neutralizing said hydrochloride with an alkali as required. Preparation processes of 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester are also disclosed.
ES553331A 1985-03-29 1986-03-24 Preparation process of alpha-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof. Expired ES8708207A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60066097A JPS61225196A (en) 1985-03-29 1985-03-29 Production of alpha-l-aspartyl-l-phenylalaninemethyl ester or hydrochloride thereof
JP60066665A JPH0751596B2 (en) 1985-04-01 1985-04-01 Process for producing α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride

Publications (2)

Publication Number Publication Date
ES8708207A1 true ES8708207A1 (en) 1987-10-16
ES553331A0 ES553331A0 (en) 1987-10-16

Family

ID=26407276

Family Applications (1)

Application Number Title Priority Date Filing Date
ES553331A Expired ES8708207A1 (en) 1985-03-29 1986-03-24 Preparation process of alpha-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof.

Country Status (8)

Country Link
US (1) US4780561A (en)
EP (1) EP0196866A3 (en)
KR (1) KR890005039B1 (en)
AU (1) AU586669B2 (en)
BR (1) BR8601385A (en)
CA (1) CA1286845C (en)
ES (1) ES8708207A1 (en)
MX (1) MX162176A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0270345B1 (en) * 1986-12-05 1992-07-22 MITSUI TOATSU CHEMICALS, Inc. Preparation of alpha-l-aspartyl-l-phenyl-alanine methyl ester or hydrohalide thereof
US4897507A (en) * 1987-07-22 1990-01-30 Ajinomoto Co., Inc. Method for producing α-L-aspartyl-L-phenylalanine derivatives
US4992552A (en) * 1988-08-31 1991-02-12 Eastman Kodak Company Process for preparation of amino acids
US5144073A (en) * 1988-08-31 1992-09-01 Hubbs John C Process for preparation of dipeptides
DE69121502T2 (en) * 1990-03-15 1997-01-16 Nutrasweet Co PROCESS FOR THE PRESENTATION OF ASPARTAM FROM A DIKETOPIPERAZINE AND NEW INTERMEDIATE PRODUCTS AND DERIVATIVES THEREFOR
JPH05117246A (en) * 1991-10-23 1993-05-14 Ajinomoto Co Inc New 2,5-dioxopiperazine compound, its production and production of alpha-l-aspartyl-l-phenylalanine methyl ester derivative
JPH05194587A (en) * 1992-01-14 1993-08-03 Ajinomoto Co Inc Method for purifying alpha-l-aspartyl-l-phenylalanine methyl ester
CN105315327A (en) * 2014-08-04 2016-02-10 南京集美新型材料研发有限公司 Method for converting 2-(5-benzyl-3,6-diketopiperazine-2-yl) acetic acid and 2-(5-benzyl-3,6-diketopiperazine-2-yl) methyl acetate
CN105315328A (en) * 2014-08-04 2016-02-10 南京集美新型材料研发有限公司 Method for removing impurities in N-alpha-L-aspartyl-L-phenylalanine 1-methyl ester

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS461370Y1 (en) * 1966-05-25 1971-01-19
JPS5113737A (en) * 1974-07-23 1976-02-03 Ajinomoto Kk Arufua ll asuparuchiru ll fueniruaraninteikyuarukiruesuteruno seizoho
US4088649A (en) * 1975-07-02 1978-05-09 Firmenich S.A. Process for preparing a diketo-piperazine
US4173562A (en) * 1976-12-27 1979-11-06 Monsanto Company Process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester
MX4704E (en) * 1976-12-27 1982-08-04 Monsanto Co IMPROVED PROCEDURE FOR THE PREPARATION OF ALPHA-L-ASPARTIL-L-PHENYLALANINE METHYL ESTER
JPS58185545A (en) * 1982-04-22 1983-10-29 Ajinomoto Co Inc Preparation of alpha-l-aspartyl-l-phenylalanine methyl ester or its hydrochloride
GB8300810D0 (en) * 1983-01-13 1983-02-16 Erba Farmitalia Aspartame synthesis
JPS59219258A (en) * 1983-05-28 1984-12-10 Ajinomoto Co Inc Preparation of alpha-l-aspartyl-l-phenylalanine methyl ester or its hydrochloride
US4618695A (en) * 1983-06-02 1986-10-21 Ajinomoto Co., Inc. Method of preparing methyl ester and its hydrochloride
JPH0613550B2 (en) * 1983-06-03 1994-02-23 味の素株式会社 Process for producing α-L-aspartyl-L-phenylalanine-lower alkyl ester
JPS59227849A (en) * 1983-06-08 1984-12-21 Ajinomoto Co Inc Crystallization and separation of l-alpha-aspartyl-l- phenylalaninemethyl ester
JPS60174799A (en) * 1984-02-21 1985-09-09 Ajinomoto Co Inc Preparation of alpha-l-aspartyl-l-phenylalaninemethyl ester

Also Published As

Publication number Publication date
BR8601385A (en) 1986-12-02
EP0196866A2 (en) 1986-10-08
MX162176A (en) 1991-04-05
EP0196866A3 (en) 1988-03-23
ES553331A0 (en) 1987-10-16
KR860007284A (en) 1986-10-10
KR890005039B1 (en) 1989-12-08
CA1286845C (en) 1991-07-23
US4780561A (en) 1988-10-25
AU5493186A (en) 1986-10-02
AU586669B2 (en) 1989-07-20

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19970303